Greenwood Holiday Rentals

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Our top choices for Greenwood holiday rentals

10.0 out of 10, Exceptional, (48 reviews)
"Comfy rooms, great layout, pretty scenery, exceeded expectations "
United States
Molly P.
The price is AU$396
includes taxes & fees
22 Mar - 23 Mar
Unique Cypress cottage, close to Charlottesville with mountain views.
10.0 out of 10, Exceptional, (5 reviews)
"The property was very clean and awesome! It met the needs of our 2 day stay with our pets. We would stay again!"
United States
Joni K.
The price is AU$206
includes taxes & fees
29 Mar - 30 Mar
Brand new serene luxury cottage just off the Brew Ridge Trail
9.8 out of 10, Exceptional, (106 reviews)
"Such a lovely cottage in a great spot!We enjoyed Crozet and time at Praha bakery, Star Hill Brewery, King Family Vineyard, and Mint Springs Park!"
United States
Polly H.
The price is AU$472
includes taxes & fees
25 Mar - 26 Mar
High Street | Walk to Everything Crozet | Pet-Friendly
10.0 out of 10, Exceptional, (104 reviews)
"We had a great time! The host was very responsive and great location! "
United States
Tess B.
The price is AU$356
includes taxes & fees
19 Mar - 20 Mar
Wintergreen. Sunset Vista Villa - Close to the ski slopes
10.0 out of 10, Exceptional, (30 reviews)
"The location was great and the place was very nice. "
United States
Amanda L.
The price is AU$209
includes taxes & fees
22 Mar - 23 Mar
Unit 5 - Cozy Lower Level Studio Suite
10.0 out of 10, Exceptional, (64 reviews)
"Everything was great! We enjoyed this stay immensely. "
United States
Deborah F.
The price is AU$414
includes taxes & fees
19 Mar - 20 Mar
Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
10.0 out of 10, Exceptional, (22 reviews)
"Very nice space. Clean, quiet, and comfortable. Host very responsive to any questions or information needs. Would definitely consider staying here again."
United States
Brian T.
The price is AU$313
includes taxes & fees
19 Mar - 20 Mar
Unit 3 - Luxury King Suite with Private Balcony
10.0 out of 10, Exceptional, (95 reviews)
"Great spot for a stay, hostess was amazing, highly recommend!!"
United States
Charles R.
The price is AU$281
includes taxes & fees
24 Mar - 25 Mar
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
10.0 out of 10, Exceptional, (98 reviews)
"Highly recommend staying at this beautiful condo! The kitchen has everything you need, the views are breath-taking, the condo is very clean, and the hosts are very communicative and helpful. Will definitely stay here again the next time we travel to the area!"
United States
Allison N.
The price is AU$367
includes taxes & fees
19 Mar - 20 Mar
Endless Mountain Top Views from All The Way Up!
10.0 out of 10, Exceptional, (69 reviews)
"Perfect location for multiple restaurants & some shopping.Very clean...enjoyable stay."
United States
Roberta F.
The price is AU$344
includes taxes & fees
19 Mar - 20 Mar
Stay in Crozet Train Suite in Downtown Crozet
9.8 out of 10, Exceptional, (30 reviews)
"Great communication from the startReturn texts the same day on any questionsGreat location for our tripVery cleanViews around property are greatNice restaurant A plus for what we neededDog friendly Thanks againHope to be back"
United States
Phil P.
The price is AU$349
includes taxes & fees
23 Mar - 24 Mar
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
10.0 out of 10, Exceptional, (14 reviews)
"Owner is excellent "
United States
Atchuthan
The price is AU$313
includes taxes & fees
19 Mar - 20 Mar
Unit 4 - Luxury King Suite with Private Balcony
9.6 out of 10, Exceptional, (149 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is AU$351
includes taxes & fees
19 Mar - 20 Mar
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
10.0 out of 10, Exceptional, (56 reviews)
"The entire home was very clean and comfortable. The property is stunning and worth exploring. "
United States
Mario
The price is AU$324
includes taxes & fees
22 Mar - 23 Mar
Peacefull, private Cabin! 140 acres,mile of river trails! 10 minutes to Rt.151!
10.0 out of 10, Exceptional, (22 reviews)
"Very clean and central to the wineries."
United States
Cynda
The price is AU$448
includes taxes & fees
22 Mar - 23 Mar
The Cottage @ Afton Mountain- Close to Wineries!

Holiday Home in Staunton

The Firefly Springhouse
9.8 out of 10, Exceptional, (51 reviews)
"The space was great for a getaway, highly recommended."
United States
Matt E.
The price is AU$164
includes taxes & fees
22 Mar - 23 Mar
The Firefly Springhouse

Cabin in Lyndhurst

Love Ridge Mountain Lodging
3.0 star property
10.0 out of 10, Exceptional, (16 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is AU$281
includes taxes & fees
19 Mar - 20 Mar
Love Ridge Mountain Lodging
10.0 out of 10, Exceptional, (20 reviews)
"The perfect stay for a wedding weekend in Waynesboro. It was very warm and accommodating and I can’t say enough good things about it. Thank you for a great weekend"
United States
Michael W.
The price is AU$265
includes taxes & fees
30 Mar - 31 Mar
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
10.0 out of 10, Exceptional, (34 reviews)
"Great"
United States
Daniel W.
The price is AU$544
includes taxes & fees
22 Mar - 23 Mar
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
10.0 out of 10, Exceptional, (56 reviews)
"The space was incredibly well furnished. Wi-Fi worked from the jump, check in was easy, host was very communicative. Great spot to stay!"
United States
Samuel M.
The price is AU$236
includes taxes & fees
19 Mar - 20 Mar
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Greenwood Hotel Reviews

Find out more about Greenwood

Everything you need to know about Greenwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenwood holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Greenwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenwood holiday rentals we have selected for you start as low as AU$157 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Greenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Greenwood?

Yes, there are holiday rentals close to the most popular sights in Greenwood, or you can select a more secluded option if you're looking for a relaxing stay. Greenwood is known for its wineries.

What are some of the best holiday rentals that Greenwood has to offer?

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious: This holiday home rental outside of Greenwood is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Greenwood?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Greenwood stay.

What’s there to see and do in Greenwood?

Explore the area and family-friendly sights such as Virginia Discovery Museum, or get out into nature at a spot like Shenandoah National Park. In the wider area, you’ll find Pollak Vineyards and King Family Vineyards.

What’s a holiday rental in Greenwood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Greenwood. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips.